A porphycene-gentamicin conjugate for enhanced photodynamic inactivation of bacteria

Ingrid Nieves, Cormac Hally, Cristiano Viappiani, Montserrat Agut, Santi Nonell

Research output: Indexed journal article Articlepeer-review

28 Citations (Scopus)

Abstract

A novel photoantimicrobial agent, namely 2-aminothiazolo[4,5-c]-2,7,12,17-tetrakis(methoxyethyl)porphycene (ATAZTMPo-gentamicin) conjugate, has been prepared by a click reaction between the red-light absorbing 9-isothiocyanate-2,7,12,17-tetrakis(methoxyethyl)porphycene (9-ITMPo) and the antibiotic gentamicin. The conjugate exhibits submicromolar activity in vitro against both Gram-positive and Gram-negative bacteria (Staphylococcus aureus and Escherichia coli, respectively) upon exposure to red light and is devoid of any cytotoxicity in the dark. The conjugate outperforms the two components delivered separately, which may be used to enhance the therapeutic index of gentamicin, broaden the spectrum of pathogens against which it is effective and reduce its side effects. Additionally, we report a novel straightforward synthesis of 2,7,12,17-tetrakis(methoxyethyl) porphycene (TMPo) that decreases the number of steps from nine to six.

Original languageEnglish
Article number103661
JournalBioorganic Chemistry
Volume97
DOIs
Publication statusPublished - Apr 2020

Keywords

  • Amphiphilicity
  • Antimicrobial resistance
  • Photodynamic therapy
  • Photosensitizer conjugates
  • Porphycene
  • Singlet oxygen

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